EP0355541A2 - Sulfures de polyarylène de poids moléculaire éléve, préparés à partir de sulfures de polyarylène et de composés dihalogénés - Google Patents
Sulfures de polyarylène de poids moléculaire éléve, préparés à partir de sulfures de polyarylène et de composés dihalogénés Download PDFInfo
- Publication number
- EP0355541A2 EP0355541A2 EP89114518A EP89114518A EP0355541A2 EP 0355541 A2 EP0355541 A2 EP 0355541A2 EP 89114518 A EP89114518 A EP 89114518A EP 89114518 A EP89114518 A EP 89114518A EP 0355541 A2 EP0355541 A2 EP 0355541A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- sulfides
- hal
- polyarylene sulfides
- poly
- arylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0286—Chemical after-treatment
- C08G75/029—Modification with organic compounds
Definitions
- the invention relates to high molecular weight polyarylene sulfides (PAS), preferably polyphenylene sulfides (PPS), made from polyarylene sulfides, preferably polyphenylene sulfide and dihalo compounds.
- PAS high molecular weight polyarylene sulfides
- PPS polyphenylene sulfides
- Polyarylene sulfides known e.g. US-PS 3354129, EP-OS 171021. They are inert, high-temperature resistant thermoplastics, which also allow a high degree of filling with glass fibers and / or other organic fillers.
- the use of these polymers, in particular polyparaphenylene sulfide (PPS), is increasing above all in areas that have hitherto been reserved for thermosets.
- a disadvantage of PAS can be unsatisfactory toughness, which can increase with increasing melt viscosity. Rapid crystallization of the PAS can also be disadvantageous for some applications, for example in the production of films. The tendency towards rapid crystallization is also lower for PAS types with a high melt viscosity.
- the invention therefore relates to high molecular weight polyarylene sulfides, preferably polyphenylene sulfides, prepared by reacting known polyarylene sulfides, preferably polyphenylene sulfide, with dihalogen compounds of the formula (I) Hal-R-Hal (I), in which R is C6 ⁇ 22-alkylene, preferably a hexamethylene, C6 ⁇ 22-cycloalkylene, C6 ⁇ 22-bis (halogenomethyl) arylene, the arylene radical preferably being an m- or p-phenylene radical or a 1,4-, 1st , 5-, 1,6-, 1,7-, 1,8-, 2,6- or 2,7-naphthylene and the arylene radicals can optionally be C1 ⁇ 6-alkyl, preferably methyl, halogen (e.g. Cl-, Br-) methyl-, C6 ⁇ 22- aryl, preferably phenyl or halogen (eg Cl
- dihalogen compounds are aromatic and aliphatic dihalogen compounds of the formula (I), for example p-xylylene dichloride, m-xylylene dichloride, 2,4- (dichloromethyl) -1,5-dimethylbenzene, 1,6-dichlorohexane, 1,12-dichlorododecane, 1 , 2,3-, and 1,2,4- and 1,3,5-tri- (chlor methyl) benzene, 1,6- and 2,6-di (chloromethyl) naphthalene and the corresponding bromine compounds. They can be used individually or as a mixture.
- the polyarylene sulfides are produced by melting together a mixture of polyarylene sulfide with 3 to 30% by weight, preferably 5 to 20% by weight, of dihalogen compound of the formula I, for example in (screw shafts) extruders, kneaders, etc.
- An aftertreatment time in the melt is 0.5 to 500 min, preferably 5 to 60 min.
- the suitable temperature for the aftertreatment according to the invention in the melt is 280 ° C. to 450 ° C., preferably 300 ° C. to 360 ° C.
- moldings made from the polyarylene sulfides to be used according to the invention can also be after-treated with dihalo compounds of the formula (I) in the solid phase at from 150 ° C. to 270 ° C.
- the process according to the invention can be carried out under inert gases (e.g. nitrogen, argon), if appropriate in vacuo up to 10 ⁇ 6 bar. Carrying out under inert gas is preferred.
- inert gases e.g. nitrogen, argon
- the polyarylene sulfides produced according to the invention can be processed into molded articles, fibers or films by the process of injection molding or extrusion.
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3828058 | 1988-08-18 | ||
| DE3828058A DE3828058A1 (de) | 1988-08-18 | 1988-08-18 | Hochmolekulare polyarylensulfide, hergestellt aus polyarylensulfiden und dihalogenaromaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0355541A2 true EP0355541A2 (fr) | 1990-02-28 |
| EP0355541A3 EP0355541A3 (fr) | 1991-01-30 |
Family
ID=6361122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19890114518 Withdrawn EP0355541A3 (fr) | 1988-08-18 | 1989-08-05 | Sulfures de polyarylène de poids moléculaire éléve, préparés à partir de sulfures de polyarylène et de composés dihalogénés |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4978729A (fr) |
| EP (1) | EP0355541A3 (fr) |
| JP (1) | JPH02103233A (fr) |
| DE (1) | DE3828058A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991008249A1 (fr) * | 1989-11-17 | 1991-06-13 | Eastman Kodak Company | Procede de preparation de copoly(arylene sulfure) presentant une quantite diminuee de radicaux de disulfure |
| EP0524827A1 (fr) * | 1991-07-24 | 1993-01-27 | Kureha Kagaku Kogyo Kabushiki Kaisha | Procédé pour la préparation de copolymère de polysulfure d'alkylène d'arylène |
| US8883960B2 (en) | 2007-01-04 | 2014-11-11 | Sk Chemicals Co., Ltd. | Polyarylene sulfide resin with excellent luminosity and preparation method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022030459A1 (fr) * | 2020-08-05 | 2022-02-10 | 株式会社クレハ | Résine de sulfure de polyphénylène modifié, composition de résine, et article moulé |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3524835A (en) * | 1963-11-27 | 1970-08-18 | Phillips Petroleum Co | Heat treatment of poly(arylene sulfide) resins |
| US3395132A (en) * | 1967-01-23 | 1968-07-30 | Dow Chemical Co | Method for crosslinking polyphenylene sulfide resins |
| US3607843A (en) * | 1969-05-16 | 1971-09-21 | Phillips Petroleum Co | Process for making poly (phenylene sulfide) polymers of increased molecular weight |
| US3839301A (en) * | 1973-07-23 | 1974-10-01 | Phillips Petroleum Co | Poly(arylene sulfide) resin heat treatment and curing |
| US4645826A (en) * | 1984-06-20 | 1987-02-24 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for production of high to ultra-high molecular weight linear polyarylenesulfides |
-
1988
- 1988-08-18 DE DE3828058A patent/DE3828058A1/de not_active Withdrawn
-
1989
- 1989-08-05 EP EP19890114518 patent/EP0355541A3/fr not_active Withdrawn
- 1989-08-07 US US07/390,229 patent/US4978729A/en not_active Expired - Fee Related
- 1989-08-15 JP JP1209725A patent/JPH02103233A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991008249A1 (fr) * | 1989-11-17 | 1991-06-13 | Eastman Kodak Company | Procede de preparation de copoly(arylene sulfure) presentant une quantite diminuee de radicaux de disulfure |
| EP0524827A1 (fr) * | 1991-07-24 | 1993-01-27 | Kureha Kagaku Kogyo Kabushiki Kaisha | Procédé pour la préparation de copolymère de polysulfure d'alkylène d'arylène |
| US5605987A (en) * | 1991-07-24 | 1997-02-25 | Kureha Kagaku Kogyo K.K. | Production process of alkylene thioether-arylene thioether copolymer |
| US8883960B2 (en) | 2007-01-04 | 2014-11-11 | Sk Chemicals Co., Ltd. | Polyarylene sulfide resin with excellent luminosity and preparation method thereof |
| US8957182B2 (en) | 2007-01-04 | 2015-02-17 | Sk Chemicals Co., Ltd. | Polyarylene sulfide resin with excellent luminosity and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0355541A3 (fr) | 1991-01-30 |
| DE3828058A1 (de) | 1990-02-22 |
| JPH02103233A (ja) | 1990-04-16 |
| US4978729A (en) | 1990-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19890805 |
|
| AK | Designated contracting states |
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| PUAL | Search report despatched |
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| AK | Designated contracting states |
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| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| 18W | Application withdrawn |
Withdrawal date: 19920714 |